title: InCl3 catalyzed highly diastereoselective [3 + 2] cycloaddition of 1,2-cyclopropanated sugars with aldehydes: a straightforward synthesis of persubstituted bis-tetrahydrofurans and perhydrofuro[2,3-b]pyrans.
abstract: A mild and efficient strategy for the construction of persubstituted bis-tetrahydrofuran and perhydrofuro[2,3-b]pyran derivatives has been developed. Persubstituted cyclization products were obtained in good to excellent yields. The [3 + 2] cycloaddition of 1,2-cyclopropanated sugars with aldehydes in the presence of InCl3 is highly diastereoselective.
authors.affiliation: Natural Products Research Centre, Chengdu Institute of Biology, Chinese Academy of Sciences , Chengdu, 610041, China, and University of Chinese Academy of Sciences , China.
authors.forename: Xiaofeng
authors.initials: X
authors.lastname: Ma
authors.forename: Qin
authors.initials: Q
authors.lastname: Tang
authors.forename: Jun
authors.initials: J
authors.lastname: Ke
authors.forename: Xinglong
authors.initials: X
authors.lastname: Yang
authors.forename: Jichao
authors.initials: J
authors.lastname: Zhang
authors.forename: Huawu
authors.initials: H
authors.lastname: Shao
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007204:Indium / Q000737:chemistry*; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D002241:Carbohydrates; D003521:Cyclopropanes; D005663:Furans; D011714:Pyrans; D007204:Indium; C020758:indium trichloride; C018674:tetrahydrofuran